Sodium Thiosulfate → Ethyl 1-formylcyclopropanecarboxylate

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Reaction Steps

Under an argon atmosphere 1-Hydroxymethyl-cyclopropanecarboxylic acid ethyl ester (5.0 g, 34.7 mmol) was dissolved in DCM (200 mL). NaHCO3 (11.7 g, 139 mmol) and Dess Martin periodinane (29.4 g, 69.4 mmol) were added. The suspension was stirred at rt for 30 min. A 1:1 solution of saturated Na2S2O3 and saturated NaHCO3 (200 mL) was added while keeping the temperature at 20° C. The mixture was stirred for 20 min followed by extraction with DCM (×2). The combined organic phases were dried (Na2SO4), filtered and concentrated to afford a crude product of 1-formyl-cyclopropanecarboxylic acid ethyl ester (5.1 g) which was used directly in the next step.

Provenance & Evidence